Anthony Dalton

As Alaric and Jo (recurring guest star Jodi O'Keefe) reluctantly participate in their bachelor and bachelorette parties, Damon and Elena discuss the ramifications from an impulsive offer that Damon makes. Unsure of what to do, Elena turns to Bonnie and Jo for advice, but is left conflicted when Bonnie raises some unanticipated concerns. When Enzo realizes Lily (recurring guest star Annie Wersching) is on a dangerous downward spiral, he asks Stefan to help intervene before it's too late. Lastly, fed up with the supernatural threats that plague their town, Matt takes his frustrations out on Tyler, while Alaric considers a life-changing piece of advice.

Teaming up with Grayson (Jackson Hurst) to supervise a law student’s suit on behalf of a computer company employee puts Jane (Brooke Elliott) at odds with her former Stanford Law School mentor. Meanwhile, Kim (April Bowlby) begins to suspect that the firm’s creditor Gina Blunt (Madchen Amick) is up to no good.